Winter Park Village Real Estate

Winter Park Village Real Estate

Welcome to Winter Park Village, a vibrant and charming subdivision nestled in the heart of Winter Park, Florida. This sought-after community, located in Orange County, is renowned for its picturesque landscapes, rich history, and a warm, welcoming atmosphere that captures the essence of Florida living.

Winter Park Village boasts a delightful blend of residential comfort and urban convenience. The area is characterized by beautifully designed homes that reflect both modern aesthetics and classic Floridian architecture. Residents enjoy spacious layouts, manicured lawns, and easy access to a variety of amenities that enhance daily life.

One of the highlights of Winter Park Village is its proximity to a plethora of shopping, dining, and entertainment options. The Village itself features an array of boutique shops, trendy restaurants, and cozy cafes, making it a perfect spot for leisurely strolls and social gatherings. Whether you're in the mood for a casual lunch or a fine dining experience, you'll find it all just moments away.

For nature enthusiasts, the nearby parks and scenic lakes provide ample opportunities for outdoor activities. Take a leisurely bike ride along the beautiful trails, enjoy a picnic by the water, or indulge in a serene afternoon of fishing. The area's lush greenery and tranquil surroundings make it an ideal place to unwind and connect with nature.

Winter Park Village is not just a place to live; it’s a community that fosters connections and celebrates the joys of life. With its unique blend of convenience, charm, and community spirit, it's no wonder that Winter Park Village is one of Florida's most desirable places to call home. Come experience the magic of Winter Park Village for yourself!

Newest Listings in Winter Park Village

$1,749,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Under Construction. Currently under construction by LUIH Luxury Homes, this exceptional new construction residence is anticipated for completion in November 2026 and brings contemporary design and elevated living to one of Winter Park's most desirable neighborhoods. Offering 4 bedrooms, 3.5 bathrooms, and 2,715 square feet of thoughtfully designed living space, the home blends clean architectural lines with warm, inviting interiors designed for both everyday living and effortless entertaining. The open-concept floor plan is filled with natural light and seamlessly connects the main living areas, creating a spacious and functional layout. Designer finishes, sophisticated details, and carefully selected materials elevate every space, while the chef-inspired kitchen serves as the heart of the home. Step outside to your private backyard retreat featuring a resort-style pool and spa, providing the perfect setting for relaxing or entertaining year-round. Ideally located just minutes from Park Avenue, residents will enjoy easy access to award-winning dining, boutique shopping, parks, golf courses, and Winter Park's vibrant cultural scene.

2525 Lafayette Avenue, Winter Park
$1,100,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Experience the perfect blend of modern luxury, thoughtful design, and an unbeatable Winter Park location in this stunning custom residence built in 2023 by acclaimed builder Odin Homes. Showcasing over two years of gentle ownership, this exceptional home lives like new and offers a rare opportunity to own a move-in-ready custom home without the wait of new construction. Designed with sophistication and functionality in mind, this 4-bedroom, 4-bath residence features spacious living areas, designer finishes, soaring ceilings, and an open-concept floor plan ideal for both everyday living and entertaining. Every detail reflects Odin Homes' renowned craftsmanship, quality construction, and attention to detail. Perfectly situated on a beautiful homesite in one of Winter Park's most desirable neighborhoods, residents enjoy access to top-rated schools including Dommerich Elementary, Maitland Middle School, and Winter Park High School. The location offers exceptional convenience just minutes from Park Avenue's renowned dining and shopping, downtown Orlando, Winter Park Village, major employers, and area attractions. Whether you're searching for a primary residence or simply want the benefits of newer construction without the construction timeline, this exceptional custom home delivers luxury, location, and lifestyle in one of Central Florida's most sought-after communities.

1404 Border Drive, Winter Park
$1,599,000
4 Beds ⋅ 4 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Positioned as one of the best values currently available in Winter Park, this exceptional residence designed by renowned architect Gary Hancock is a masterclass in craftsmanship, architecture, and timeless elegance. From the moment you arrive, the home commands attention with a breathtaking facade defined by graceful archways and refined architectural symmetry. Every exterior line and material selection has been intentionally chosen to create a presence that feels both bold and enduring, setting this residence apart as something truly exceptional. Inside, the home unfolds into a light-filled interior where design and livability coexist seamlessly. Ten-foot ceilings, level 5 drywall, and an abundance of expansive windows allow natural light to pour into every space, illuminating the impeccable finishes and creating an airy, sophisticated atmosphere throughout. Upgraded designer light fixtures add warmth and character, while the open-concept layout is anchored by a stunning living area centered around a refined fireplace, offering a natural gathering space that feels both intimate and grand. Flowing effortlessly from the living room, the dining area opens through elegant doors to the outdoor entertaining spaces, beautifully blending indoor and outdoor living. At the heart of the home, the chefs kitchen is as visually striking as it is thoughtfully designed. Custom cabinetry, sleek quartz countertops, a paneled refrigerator, and a premium induction range, reflect the builders uncompromising commitment to quality, performance, and clean modern design. The primary suite is a private retreat, highlighted by a spa-inspired bath with a freestanding soaking tub, an expansive walk-in shower, and a beautifully designed walk-in closet with direct access to the laundry room for effortless everyday living. Each secondary bedroom continues the theme of elevated design, offering generous proportions, abundant natural light, and elegantly appointed en-suite baths that ensure comfort and privacy for family and guests alike. Outdoors, the home reveals another level of thoughtful craftsmanship. A covered patio with a fully equipped summer kitchen overlooks a sparkling pool and expansive backyard, creating a setting equally suited for quiet evenings or lively gatherings. What truly defines this residence is the extraordinary level of craftsmanship throughout. No detail has been overlooked, no finish treated as an afterthought, and no design decision made without intention. This is a home that feels as impressive in its execution as it does in its presence.

2430 Chantilly Avenue, Winter Park
$589,000
3 Beds ⋅ 2 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Tremendous value in the land. Well cared for vintage Winter Park home that has 3 BEDROOM and two bath rooms. Potential to remodel, improve and expand or simply tear down to build a new custom home. However, this home is move in ready! There is not an HOA. 1343 total square feet and 1186 heated square feet. Newer DUAL-PANE WINDOWS! New HVAC system in NOvember 2025. Home was replumbed in 2024. SEPTIC PUMP OUT, OCT 2025. No carpeting instead there is SOLID FLOORING THROUGHOUT: WOOD PARQUET, TILE, LUXURY VINYL PLANK. The kitchen has been updated with SOLID WOOD KITCHEN CABINETS + GRANITE COUNTER TOPS and newer MATCHING APPLIANCES. The home has INDOOR WASHER/DRYER and a working fireplace. The back yard is FULLY FENCED. Local top rated CITY OF WINTER PARK SCHOOLS. And CITY OF WINTER PARK UTILITIES. The land, the lot have a fantastic upside. BOTH NEXT DOOR (WEST SIDE) AND REAR (NORTH SIDE) NEIGHBORING LOTS HAVE BEEN EMPTY FOR SEVERAL YEARS. This is a great investment and the property itself offers excellent rental income. Think "down the road" value + immediate return value.

1319 Bessmor Road, Winter Park
Start Your Search